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N-Phenyl-1-naphthalinamin
PANA · N-phenylnaphthalen-1-amine · PHENYL ALPHA NAPHTHYLAMINE · 1-Naphthalenamine, N-phenyl- · Phenylnaphthylamine · N-Phenyl-1-naphthalenamine · T351 · amoco32
Identifikatoren & physikalische Daten
| CAS No. | 90-30-2 |
|---|---|
| Summenformel | C16H13N |
| Durchschnittliche Molmasse | 219,28 g/mol |
| Monoisotopische Masse | 219,10479942 g/mol |
| SMILES | c1ccc(Nc2cccc3ccccc23)cc1 |
| InChIKey | XQVWYOYUZDUNRW-UHFFFAOYSA-N |
| PubChem CID | 7013 |
| ChEMBL | CHEMBL170408 |
| ChEBI | CHEBI:34876 |
| EC No. | 201-983-0 |
| DTXSID | DTXSID2025892 |
| Lokaler Name | N-Phenyl-1-naphthalinamin |
Chemische & physikalische Eigenschaften
| XLogP | 4,4 |
|---|---|
| Polarare Oberfläche (TPSA) | 12 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 17 |
| Formalladung | 0 |
| Komplexität | 232 |
| Stoffklassen | Nitrogen Compounds -> Naphthylamines |
| SpringerMaterials Properties | Boiling point |
| LogP (Verteilungskoeffizient) | log Kow = 4.20 |
| Geruch | Amine-like |
| Dichte | Relative density (water = 1): 1.21,1 g/cm3 |
| Color/Form | Prisms or needles from alcoholleaflets from ligroin.Tan to purple crushed solid or crystals.White to yellowish crystalsIn its pure form crystallizes into lemon yellow prisms or needles ... marketed in the form of brown to dark violet crystals or light brown to light violet granules |
| Löslichkeit | less than 1 mg/mL at 70 °F (NTP, 1992)Soluble in ethanol, ethyl ether, benzene, carbon tetrachloride, chloroform, acetic acid.In water, 60 mg/L @ 25 °CSolubility in water: none1.5 [ug/mL] (The mean of the results at pH 7.4)0.003g/linsoluble |
| Flammpunkt | Flash point > 200 °C>200°C |
| Siedepunkt | 635 °F at 528 mmHg (NTP, 1992)335 °C @ 558 mm Hg226 °C15 mm Hg(lit.) |
| Decomposition | When heated to decomposition it emits toxic fumes of /nitrogen oxides/. |
| Schmelzpunkt | 144 °F (NTP, 1992)61 °C62-63 °C60-62 °C(lit.) |
| Dampfdruck | 0.00000829 [mmHg]1.13X10-5 mm Hg @ 25 °C /Extrapolated/0.504 hPa (150 °C) |
| Brechungsindex | 1.7020 (estimate) |
| Lagerbedingungen | Store below +30°C. |
| Aggregatzustand | Crystals or Flakes |
| pKa (Säurekonstante) | 0.78±0.30(Predicted) |
| Farbe | Pinkish to light brown |
| BRN | 2211174 |
| Henry-Konstante | 7.0×101 mol/(m3Pa) at 25℃, HSDB (2015) |
| Stabilität | Stable. Incompatible with strong oxidizing agents, strong acids. |
| InChI | 1S/C16H13N/c1-2-9-14(10-3-1)17-16-12-6-8-13-7-4-5-11-15(13)16/h1-12,17H |
| InChIKey | XQVWYOYUZDUNRW-UHFFFAOYSA-N |
| SMILES | N(c1ccccc1)c2cccc3ccccc23 |
| CAS Datenbank | 90-30-2(CAS DataBase Reference) |
| NIST chemische Informationen | 1-Naphthyl phenyl amine(90-30-2) |
| EPA chemische Informationen | N-Phenyl-1-naphthylamine (90-30-2) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 0.3% (5 of 1663) of reports.WarningH302 (90.3%): Harmful if swallowed [Warning Acute toxicity, oral]P260, P261, P264, P270, P272, P273, P280, P301+P317, P302+P352, P319, P321, P330, P333+P317, P362+P364, P391, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 1663 reports by companies from 50 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Danger |
|---|---|
| Regulatorische Informationen | Chemical: 1-Naphthalenamine, N-phenyl-1-Naphthalenamine, N-phenyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1-Naphthalenamine, N-phenyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 11-04-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/180781-Naphthylamine, N-phenyl-: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | IMAP assessments - 1-Naphthalenamine, N-phenyl-: Human health tier I assessment |
| DOT-Kennzeichnung | Class 9 |
| Brandgefahren | Flash point data for this compound are not available. It is probably combustible. (NTP, 1992)Combustible. Gives off irritating or toxic fumes (or gases) in a fire. |
| Gesundheitsgefahren | ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits toxic fumes. (NTP, 1992) |
| Gefahrenübersicht | Danger of skin sensitization[MAK] Can induce methemoglobinemiaMay cause skin sensitization[ICSC] An irritant[MSDSonline] |
| Reaktive Gruppe | Amines, Phosphines, and Pyridines |
| Special Reports | International Programme on Chemical Safety's Concise International Chemical Assessment Documents. Number 9: N-Phenyl-1-naphthylamine (1998). Available from http://www.inchem.org/documents/cicads/cicads/cicad9.htm as of July 26, 2004. |
| TSCA-Anforderungen | Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329.Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. N-Phenyl-1-naphthylamine is included on this list. |
| Reactivity Profile | N-PHENYL-1-NAPHTHYLAMINE neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides. |
| Chemical Dangers | Decomposes on burning. This produces toxic fumes including nitrogen oxides. |
| Air and Water Reactions | May be sensitive to prolonged exposure to air. Insoluble in water. Napthyl amines can be slowly hydrolyzed, releasing NH3 as a byproduct [N.L. Drake, Org. React. 1, (1942), 105]. |
| Brandbekämpfung | Fires involving this compound can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)Use water spray, powder, foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water. |
| Erste-Hilfe-Maßnahmen | Fresh air, rest. Refer for medical attention.Remove contaminated clothes. Rinse skin with plenty of water or shower.First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Rinse mouth. Refer for medical attention . |
| Erste Hilfe | EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. |
| Sichere Lagerung | Well closed. Store in an area without drain or sewer access. Provision to contain effluent from fire extinguishing. |
| Expositionsschutz und Persönliche Schutzausrüstung | 2.0 [mg/m3], inhalable fraction[German Research Foundation (DFG)] |
| Brandbekämpfungsverfahren | Powder, water spray, foam, carbon dioxide. ...In case of fire: keep drums, etc., cool by spraying with water. /from table/ |
| Lagerbedingungen | /Keep/ well closed. |
| Reinigungsverfahren | Sweep spilled substance into sealable containers. Carefully collect remainder, then remove to safe place. Do NOT let this chemical enter the environment. |
| Freisetung ohne Brand | SMALL SPILLS AND LEAKAGE: If a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. |
| Entsorgungsverfahren | SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations. |
| Verschüttetes entsorgen | Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered sealable containers. Carefully collect remainder. Then store and dispose of according to local regulations. |
| Isolation and Evacuation | Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: |
| Ökotoxizitätswerte | EC50 Tetrahymena pyriformis (inhibition of cell proliferation) 2 mg N-phenyl-1-naphthylamine/L/48 hrstatic, solubilizer: acetoneLC50 Daphnia magna 0.06 mg/L/21 daysemi-staticLC50 Goldfish 4.4 mg/L/48 hr /Conditions of bioassay not specified in source examined/LC50 Xenopus laevis (Clawed frog, larvae) 2.3 mg/L/48 hr /Conditions of bioassay not specified in source examined/ |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 4,600(SRC), determined from a log Kow of 4.20(2) and a regression-derived equation(3), indicates that N-phenyl-1-naphthylamine is expected to have slight mobility in soil(SRC). The pKa of N-phenyl-1-naphthylamine is 4.93 at 25 °C(4) indicating that this compound will partially exist in the cation form in the environment(5). Volatilization of N-phenyl-1-naphthylamine from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.4X10-7 atm-cu m/mole(SRC), derived from its vapor pressure, 1.13X10-5 mm Hg(6), and water solubility, 60 mg/L(7). N-Phenyl-1-naphthylamine is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(7). A 17% CO2 evolution when incubated in temperate soil after 11 days(8) indicates that N-phenyl-1-naphthylamine biodegradation in soil is not a major environmental fate process(SRC).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 4,600(SRC), determined from a log Kow of 4.20(2) and a regression-derived equation(3), indicates that N-phenyl-1-naphthylamine is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.4X10-7 atm-cu m/mole(SRC), derived from its vapor pressure, 1.13X10-5 mm Hg(4), and water solubility, 60 mg/L(5). According to a classification scheme(6), a BCF range of 427 to 2,730(5), suggests bioconcentration in aquatic organisms is high to very high(SRC). Measured photochemical degradation half-lives in water of 8.4 and 5.7 minutes have been reported(7). Biodegredation in water is moderate(SRC) as indicated by a theoretical BOD in freshwater of 50% after 10 days(8).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), N-phenyl-1-naphthylamine, which has an extrapolated vapor pressure of 1.1X10-5 mm Hg at 25 °C(2), is expected to exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase N-phenyl-1-naphthylamine is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC)the half-life for this reaction in air is estimated to be 1 hr(SRC), calculated from its rate constant of 3.5X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase N-phenyl-1-naphthylamine may be removed from the air by wet and dry deposition(SRC). Based on its uv adsorption spectrum, direct photolysis of this compound is expected(4). |
| Unerwünschte Wirkungen | Methemoglobinemia - The presence of increased methemoglobin in the bloodthe compound is classified as secondary toxic effect |
| Expositionspfade | The substance can be absorbed into the body by inhalation of its aerosol, through the skin and by ingestion. |
| Ökotoxizitätsauszüge | /AQUATIC SPECIES/ Sublethal N-phenyl-1-naphthylamine concentrations of approximately 5.2 and 5.6 mg/L had teratogenic effects on embryos and larvae, respectively, of the clawed frog (Xenopus laevis). Concentrations above 6.2 mg/L were lethal (100% death of larvae within 24 hr) for both. ...For larvae of the leopard frog (Rana pipiens), a 48-hr LC100 of 5 mg/L was reported ... |
| Signs and Symptoms | Blue lips, fingernails and skin. Confusion. Convulsions. Dizziness. Headache. Nausea. Unconsciousness.MAY BE ABSORBED!See Inhalation. |
| Effluent Concentrations | N-Phenyl-1-naphthylamine was identified, not quantified in wastewater samples being released into the Providence River, Massachusetts(1,2). |
| ICSC Environmental Data | The substance is very toxic to aquatic organisms. Bioaccumulation of this chemical may occur in fish. It is strongly advised not to let the chemical enter into the environment. |
| Soil Adsorption/Mobility | The Koc of N-phenyl-1-naphthylamine is estimated as 4,600(SRC), using a measured log Kow of 4.2(1), and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that N-phenyl-1-naphthylamine is expected to have slight mobility in soil. The pKa of N-phenyl-1-naphthylamine is 4.93 at 25 °C(4) indicating that this compound will partially exist in the cation form in the environment(3) Since N-phenyl-1-napthylamine exists in the protonated form, it will adsorb more strongly to organic carbon and clay than its neutral counterparts(5). |
| Human Toxicity Excerpts | /HUMAN EXPOSURE STUDIES/ N-Phenyl-1-naphthylamine, mixed with oil or water, was not irritating when applied to the skin of volunteers (no data on concentrations available). Skin eczema in workers has been attributed to repeated exposure to high levels of N-phenyl-1-naphthylamine, possibly in combination with other substances. Reportedly, the content of N-phenyl-1-naphthylamine in a special antirust oil had to be lowered from 2% to 0.5% because of skin problems. Workers, who did not wear gloves, were exposed during the packaging of bearing rings covered with antirust-oil containing N-phenyl-1-naphthylamine./SIGNS AND SYMPTOMS/ Acute hazards/Symptoms of Inhalation exposure: Blue lips or finger nails. Blue skin. Confusion. Convulsions. Dizziness. Headache. Nausea. Unconsciousness. /from table//CASE REPORTS/ At a manufacturing firm making rollers for conveyor belts, the lubricant used was a fire resistant (FR) grease. Alvania Grease-RA was also used. It appeared that three employees were suffering from contact dermatitis and were patch tested. Two were allergic to phenyl-alpha-naphthylamine (PAN) which was present in both greases at 1%. There was no cross reactivity demonstrated with other naphthylamines. Brief histories of the two workers were provided. One was a 58 yr old welder and the other was a 61 yr old roller assembly worker. Despite improved protection for each of these workers, they continue to be afflicted by eczema. One required regular moderately potent topical applications of a steroid to control the condition. Both were diagnosed as having developed allergic contact dermatitis from the FR and Alvania greases as a result of sensitization to PAN, and also aryl phosphate ester mix in the second case. The authors note that testing with the routinely available phenyl-beta-naphthylamine and di-beta-naphthyl-p-phenylenediamine is not an adequate screen for detecting PAN sensitivity. They emphasize the risk of extrapolating data from animal models./CASE REPORTS/ N-Phenyl-1-naphthylamine was also reported to have sensitizing properties in humans. Case-studies on patients with contact dermatitis, potentially associated with occupational exposure to N-phenyl-1-naphthylamine in greases or oils, have been identified. The majority of these patients also had a positive reaction to other substances in the test series, such as mercaptobenzothiazole or p-phenylenediamine. Lower incidences were reported in patients with past exposure to rubber materials. Because of the chemical's incorporation into the polymer matrix, exposure to N-phenyl-1-naphthylamine in rubber materials is assumed to be lower than exposure from greases or oils./EPIDEMIOLOGY STUDIES/ An increased occurrence of cancers in a small packaging unit in a Swedish engineering company was reported in a cohort study. Between 1954 and 1957, a special anticorrosive oil, which contained 0.5% N-phenyl-1-naphthylamine in addition to other chemicals, had been used in this unit. In 12 of 78 women in this unit (group A: 78 women/20 men), cancers were diagnosed between 1964 and 1973 in several organs (predominantly the uterus and ovary). The staff performing the actual packaging, and thus in contact with the oil, were mainly women. Morbidity and mortality from cancer were 3.1- and 3.5-fold higher, respectively, than expected, based upon age-specific and sex-specific data from the Swedish Cancer Register (the standard cancer rates for the period 1974-1976 were estimated on the basis of the 1973 rate). In the males of group A, no significant differences were established. In another unit (reference group B: 25 women/8 men) where anticorrosive oil without N-phenyl-1-naphthylamine had been used, morbidity and mortality from cancer were not elevated. This was also true for reference group C (8 women/23 men), from units that had been in contact with N-phenyl-1-naphthylamine-containing anticorrosive oil for a short period of time only, because they had demonstrated allergic reactions. The authors concluded that, apart from exposure to N-phenyl-1-naphthylamine, the formation of N-nitroso-N-phenyl-1-naphthylamine from sodium nitrite originating from the packaging paper used may be a possible explanation for the increased frequency of cancer in group A. |
| Artificial Pollution Sources | N-Phenyl-1-naphthylamine's production and use as an antioxidant in various lubrication oils and as both a protective agent and antioxidant in rubber and rubber mixtures for various products, including tires(1) may result in its release to the environment through various waste streams(SRC). |
| Environmental Biodegradation | AEROBIC: N-Phenyl-1-naphthylamine, present at 100 mg/L, reached 0% of its theoretical BOD in 2 weeks using an activated sludge inoculum at 30 mg/L and the Japanese MITI test(1). In contrast, another test showed a 50% theoretical BOD in 5 days using a freshwater inoculum(2). Using an activated sewage inoculum, N-phenyl-1-naphthylamine (concentration of 2 ug/g) reached 70% of its theoretical BOD in 2 days(2). In screening tests, N-phenyl-1-naphthylamine present in a concentration of 2 ug/mL, reached 50% of its theoretical BOD in 10 days in Oneida Lake, NY water(2). Using acclimated lake water supplemented with nutrient broth, N-phenyl-1-naphthylamine (concentration of 2 ppm) reached 90% of its theoretical BOD after 10 days. N-Phenyl-1-naphthylamine was observed to degrade in a soil study, based on carbon dioxide evolution at rates of 7 and 17% 14CO2 evolution (40 nCi of 14CO2%-test compound/g soil) after 2 and 11 days, respectively(2). |
| Wassergefährdungsklasse (WGK) | 2 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | 3077 |
| Zollcode | 29214980 |
| RTECS-Nr. | QM4500000 |
| R-Sätze (R) | 22-36/37/38-50/53-43 |
| Toxizität | LD50 orally in Rabbit: > 2000 mg/kg |
| Gefahrensymbole | Xn,N |
| Sicherheitshinweise (S) | 26-36-61-37/39-29-60-36/37 |
| Gefahrenklasse | 9Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Skin Sens. 1BSTOT RE 2 |
| Verpackungsgruppe | III |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrstoffdaten | 90-30-2(Hazardous Substances Data) |
| Selbstentzündungstemperatur | >500 °C |
Anwendungen & Verwendung
Verwenden
N-Phenyl-1-naphthylamine can be used as fluorescent probe for the determination of critical micelle concentration of surfactants. N-Phenyl-1-naphthylamine was used in a method for determination of the concentration of organolithium and organomagnesium reagents. N-Phenyl-1-naphthylamine was used as hydrophobic probe to study the phase transitions of membrane lipids in whole cells .